P
US6946565B2ExpiredUtilityPatentIndex 89

Process for the preparation of an indole derivative

Assignee: SMITHKLINE BEECHAM PLCPriority: Jul 16, 1998Filed: Jan 30, 2003Granted: Sep 20, 2005
Est. expiryJul 16, 2018(expired)· nominal 20-yr term from priority
Inventors:FEDOULOFF MICHAELSTRACHAN JOHN BRYCE
C07D 209/42
89
PatentIndex Score
22
Cited by
11
References
11
Claims

Abstract

A process for the preparation of methyl 2-(3-chloropropoxy)-indole-3-carboxylate, which comprises reacting a 3-chloro-3-carboxylate indole compound with 3-chloropropanol in the presence of an acid having a pKa of from 0 to 2.

Claims

exact text as granted — not AI-modified
1. A process for the preparation of methyl 2-(3-chloropropoxy)-indole-3-carboxylate, namely the compound of formula (B): 
                 
 which process comprises reacting a compound of formula (C) 
                 
 
 
       with 3-chloropropanol in the presence of an acid having a pKa of from 0 to 2, wherein the acid is trichloroacetic acid, dichloroacetic acid and/or trifluoroacetic acid. 
     
     
       2. A process as claimed in  claim 1  in which the reaction is effected in an organic solvent. 
     
     
       3. A process as claimed in  claim 2  in which the organic solvent is dichloromethane or chloroform. 
     
     
       4. A process as claimed in  claim 3  wherein the reaction is effected using a catalytic amount of the acid. 
     
     
       5. A process for the preparation of methyl 2-(3-chloropropoxy)-indole-3-carboxylate, namely the compound of formula (B): 
                 
 
       which process comprises reacting a compound of formula (C) 
                 
 with 3-chloropropanol in the presence of an acid having a pKa of from 0 to 2, wherein the reaction is effected in an organic solvent at a temperature in the range −20° C. to +10° C.  
 
     
     
       6. A process as claimed in  claim 5  in which the acid is trichloroacetic acid, dichloroacetic acid and/or trifluoroacetic acid. 
     
     
       7. A process as claimed in  claim 5  in which the acid is trichloroacetic acid. 
     
     
       8. A process as claimed in  claim 5  in which the organic solvent is dichloromethane or chloroform. 
     
     
       9. A process as claimed in  claim 6  in which the organic solvent is dichloromethane or chloroform. 
     
     
       10. A process as claimed in  claim 5  wherein the reaction is effected using a catalytic amount of the acid. 
     
     
       11. A process as claimed in  claim 9  wherein the reaction is effected using a catalytic amount of the acid.

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